Find Hotels with Bars in Pittsfield, MA

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Check availability on Pittsfield Hotels with Bars

Our top choices for Pittsfield hotels with a bar

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1007)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is NT$3,078
NT$3,438 total
includes taxes & fees
Jan 9 - Jan 10
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (660)
" Nice staff - beautiful hotel!"
United States
MARY
The price is NT$4,017
NT$4,487 total
includes taxes & fees
Jan 23 - Jan 24
Hilton Garden Inn Lenox Pittsfield

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (811)
"Great staff, room was huge and comfortable. "
United States
Cameron
The price is NT$4,680
NT$5,228 total
includes taxes & fees
Jan 6 - Jan 7
Hotel On North

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is NT$4,366
NT$4,877 total
includes taxes & fees
Jan 19 - Jan 20
Element Lenox Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is NT$7,915
NT$9,894 total
includes taxes & fees
Jan 26 - Jan 27
Prospect Berkshires

Cozy Corner Motel

Cozy Corner Motel
2.0 star property
Williamstown
9.2 out of 10, Wonderful, (889)
"Clean, Great Staff, Quiet"
United States
john
The price is NT$2,177
NT$2,575 total
includes taxes & fees
Feb 1 - Feb 2
Cozy Corner Motel

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is NT$3,177
NT$3,549 total
includes taxes & fees
Jan 19 - Jan 20
The Yankee, Trademark Collection by Wyndham

Willows Motel Williamstown

Willows Motel Williamstown
2.0 star property
Williamstown
9.0 out of 10, Wonderful, (999)
"Convenient location & a clean room"
United States
Stephanie
The price is NT$2,403
NT$2,684 total
includes taxes & fees
Jan 6 - Jan 7
Willows Motel Williamstown

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (816)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is NT$3,534
NT$4,561 total
includes taxes & fees
Jan 15 - Jan 16
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (832)
"Great hospitality and beautiful design. Our family had a great time!"
United States
Alison
The price is NT$3,444
NT$3,847 total
includes taxes & fees
Jan 8 - Jan 9
Berkshires Untold
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Pittsfield Hotel Reviews

Frequently asked questions

Searching for hotels with bars in Pittsfield?
Pittsfield offers 75 hotels and other lodging options to choose from, and likely many will have a bar where you can enjoy a beer after a day out and about exploring. While you're here, consider a visit to Berkshire Museum and Colonial Theater.
What are the best hotels with bars in Pittsfield?
Here's some of the top Pittsfield accommodations with bars: Holiday Inn & Suites Pittsfield-Berkshires by IHG: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Hotel On North: Enjoy the bar, free WiFi, and free parking. Hilton Garden Inn Lenox Pittsfield: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking.
What is there to do in Pittsfield?
If you have time to explore, consider visiting Berkshire Museum, Colonial Theater, and Bousquet Ski Area, and then find a cozy spot for a nightcap. Other places to see include Hancock Shaker Village and Housatonic River. Pittsfield is appreciated for its entertainment venues.
When is the best time to visit Pittsfield?
Visiting local bars in Pittsfield is more fun when you know what the weather holds. These temperatures and rainfall averages can help you determine the best time for bar hopping. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
How can I get to Pittsfield and around the area?
You might want to make the most of these transportation choices in and around Pittsfield: Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.

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